Diethyl Ether → HCID 21414264, compound

HRID 442325Notes

Reaction equation

HRID 442325 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:27][N:28]1[C:34]2[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:33]=2[CH:32]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[NH:31][CH2:30][C:29]1=[O:46]>C(N(CC)CC)C.O1CCCC1>[CH3:27][N:28]1[C:34]2[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:33]=2[CH:32]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:31]([C:13](=[O:15])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:30][C:29]1=[O:46]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14349BenzyloxycarbonylglycineHCID 24819Phosphorus pentachlorideHCID 30819844,5-Dihydrodiazepam

Product 1

HCID 21414264HCID 21414264, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

2.8 g. (13.4 mmoles) of benzyloxycarbonyl-glycine are suspended in 27 ml. of dry ether, and 3 g. (15 mmoles) of phosphorous pentachloride are added in portions to the suspension at 0° C. The mixture is stirred for 20 minutes, and thereafter a solution of 2.86 g. (10 mmoles) of 1-methyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 15 ml. of dry tetrahydrofuran containing 9 ml. of triethylamine is added dropwise to the obtained solution. The reaction mixture is stirred in an ice bath for 6 hours, and evaporated to dryness under reduced pressure. The oily residue is dissolved in 100 ml. of chloroform, the chloroform solution is washed with 3×50 ml. of water, 1×50 ml. of sodium bicarbonate solution and with water again, dried, and evaporated to dryness under reduced pressure. The oily residue is covered with ether, upon which is solidifies. 4.28 g. (90 %) of 1-methyl-4-(N-benzyloxycarbonyl-aminoacetyl)-5-phenyl- 7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are obtained; m.p.: 158°-160° C. (after recrystallization from ethanol), Rf2 = 0.60. Analysis: Calculated for C26H24O4N3Cl (M = 477.93): C: 65.2 % H: 5.1 % N: 8.8 % Found: C: 65.5 % H: 4.9 % N: 8.9 %

Workup

  1. stirringThe reaction mixture is stirred in an ice bath for 6 hours
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe oily residue is dissolved in 100 ml
  4. washof chloroform, the chloroform solution is washed with 3×50 ml
  5. dry with materialof sodium bicarbonate solution and with water again, dried
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6016089759d540c49d99a27268b2847e
Source dataset
uspto-grants-1977_08
Patent number
US04045433

Reaction notes

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